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Sodium borohydride → 2,3,5,6-Tetrafluoro-4'-hydroxymethyl-biphenyl-4-carboxylic acid methyl ester

HRID 1470662
Notes
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Reaction equation

HRID 1470662 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([F:11])=[C:9]([F:12])[C:8]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[O:20])=[CH:15][CH:14]=2)=[C:7]([F:21])[C:6]=1[F:22])=[O:4].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[C:6]([F:22])=[C:7]([F:21])[C:8]([C:13]2[CH:14]=[CH:15][C:16]([CH2:19][OH:20])=[CH:17][CH:18]=2)=[C:9]([F:12])[C:10]=1[F:11])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 580739392,3,5,6-Tetrafluoro-4'-formyl-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 580739242,3,5,6-Tetrafluoro-4'-hydroxymethyl-biphenyl-4-carboxylic acid methyl esterYield 86.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-10 °C

Procedure

2,3,5,6-Tetrafluoro-4′-formyl-biphenyl-4-carboxylic acid methyl ester (1.26 g, 4.03 mmol) was dissolved in methanol (30 mL) and cooled to −10° C. Sodium borohydride (0.76 g, 20.19 mmol) was added portion wise and reaction mixture stirred by maintaining the same temperature. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was concentrated to dryness. The obtained residue was redissolved in ethyl acetate (50 mL) and washed with water (20 mL×2) followed by brine, dried over anhydrous sodium sulphate and concentrated to get colorless solid (1.1 g, 86.75%).

Workup

  1. customreaction mixture
  2. temperatureby maintaining the same temperature
  3. concentrationAfter completion, the reaction mixture was concentrated to dryness
  4. dissolutionThe obtained residue was redissolved in ethyl acetate (50 mL)
  5. washwashed with water (20 mL×2)
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ca523cb9a0a64791bc519b4763ff9765
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09006454B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes